Proper Insurance vs Steadily

Proper Insurance’s standout feature is business income coverage on an “actual loss sustained” basis with no time limit — protection continues for as long as it reasonably takes to repair or rebuild, not capped at 12 months like many business owner policies. It also removes the vacancy clause entirely, meaning you’re covered whether the property is rented, vacant, or used by you or family.

Steadily’s coverage is solid landlord insurance with STR add-ons — dwelling, $1M+ liability, loss of rent and personal property — but it’s built as a flexible product across rental durations rather than a purpose-written, all-in-one STR replacement policy the way Proper’s is.

Steadily quotes and binds coverage in minutes through a self-serve online process — a genuinely fast experience that scored a perfect 10/10 on setup in our testing, across 48 states.

Proper Insurance has no self-serve pricing; hosts must request a personalized quote, which takes longer but reflects the underwriting depth (Lloyd’s of London, Concert Specialty) behind a fully custom replacement policy rather than a templated landlord product.

Proper Insurance premiums typically run $1,000-3,000/year for a single-family STR, varying with property value, location and risk factors — no fixed list price, quote-based only.

Steadily reports an average of $1,377/year for STR policies specifically, positioning it competitively within the same general range, with the added benefit of an instant online quote to confirm your actual number before committing.

Steadily integrates directly with Guesty for in-platform quoting and binding — a real workflow advantage for hosts already managing their portfolio through that PMS.

Proper Insurance is a traditional insurance product with no PMS or OTA integrations; you manage your policy entirely separately from your booking and operations stack.

Steadily’s landlord insurance flexes across short-term, mid-term and long-term rental use — useful if your portfolio mixes rental strategies or you switch a property between STR and long-term letting seasonally.

Proper Insurance is purpose-written for short-term rental use specifically. That focus is also its strength — the policy language and endorsements (guest-caused damage, bed bugs with lost income, liquor/pet/pool liability) are STR-specific in ways a more flexible, general landlord policy may not fully match.

Proper Insurance is underwritten by Lloyd’s of London and Concert Specialty — A-rated paper with a long track record in the STR insurance space, reflected in its 9/10 trust/uptime score.

Steadily holds a strong 4.4-4.9/5 Trustpilot rating for service and speed, but its own review flags some abrupt cancellation and underwriting complaints, and non-admitted policies in some states offer less regulatory protection than admitted carriers. It’s a newer insurer with a shorter track record than Proper.